


Chuck Shurley is a DILF.

by thedropoutandthejunkie (elenajames)



Series: Chuck Shurley is a DILF [1]
Category: Supernatural
Genre: Age Difference, Alcohol, Artist Castiel, Felching, Implied Dean/Gadreel, Implied Debriel, Implied/Referenced Underage Sex, Multi, Rough Sex, implied angelcest, implied wincest, non hunting AU
Language: English
Status: Completed
Published: 2016-03-23
Updated: 2016-03-23
Packaged: 2018-05-28 15:51:37
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,467
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6334984
Author URL: https://archiveofourown.org/users/elenajames/pseuds/thedropoutandthejunkie
Summary: <blockquote class="userstuff">
              <p>It was one thing to screw around with your best friend and his brothers (and your brother). It was another thing entirely to want to screw around with his father.</p>
            </blockquote>





	Chuck Shurley is a DILF.

**Author's Note:**

> Inspired by [this post](http://homo-pink.tumblr.com/post/141487953822).  
> Dedicated to wingedwincest, castielslittleabomination, and bendoverandbiteyourgag for letting me rant about this fic.

Dean never meant for Cas to find out about his . . . fantasies about Chuck. It was one thing to screw around with your best friend and his brothers (and your brother). It was another thing entirely to want to screw around with his  _ father _ . 

Truth is, Dean’s not sure what attracts him to the man. Chuck’s scruffy and unkempt, every bit the flighty creative stereotype. He’s nervous around Dean and doesn’t have much control over his children - not that he needs any. All the boys in the Shurley clan are bizarre and bizarrely well-behaved. 

Well, at least in public. 

Dean had heard stories throughout middle school about Gabriel and the wild parties he’d been a part of. Gadreel - the oldest brother - was more elusive, but whispers about his rather extensive sexual history still circulated. Then there was  Cas. Pierced and artsy, Cas sometimes comes to school dressed like a hobo, and other days he looks like a model. (Well, Dean always thinks Cas looks like a model, but he’s seen and touched what’s under all those layers.) 

All three brothers are every bit as adventurous as the rumors said, Dean learns. He’s spent more than one weekend in the Shurley household, (and in various beds therein) until his presence was considered an expected thing. 

It slips out on one such weekend, when Dean’s high on sex and drunk on liquor, sprawled out on Cas’ bed while the other boy does sketch after sketch of Dean’s naked form. 

“He’s kinda hot, you know?” 

“Hmm?” 

“Chuck. Your dad. In like, a scruffy older guy kinda way.” 

For the first time in twenty minutes, the scratching of Cas’ charcoal stops. There’s a smudge along his cheekbone when he looks up, contrasting against pale skin and highlighting blue eyes. 

“He’s my father.” 

“And? You’ve told me about your brothers man, this isn't that different.” 

Cas looks thoughtful, if a bit annoyed at Dean’s point. “He’s old.” 

Dean laughs, rolling onto his hands and knees to crawl over to Cas, gently setting the sketchbook and charcoal aside as he climbs into the other boy’s lap. “I forget you have a thing for younger men, not older.” 

“And I forget that you’re a hedonist,” Cas words are stern, but he’s smiling crookedly despite himself, leaning up to meet Dean halfway for a kiss. Dean rocks his hips encouragingly, bumping their half-mast erections together. Neither of them are getting off again, but Dean loves making out with Cas like this. No one kisses quite like Cas does. 

They wake up sore-headed, trying to sneak down the stairs only to be greeted by an amused Chuck sipping coffee over his morning paper. 

Cas, as he often does, wrangles Dean into helping him make breakfast. Bacon, eggs, hashbrowns, gravy - all nice and greasy to assuage their hangovers. Chuck murmurs a thank you when Cas makes him a plate, and the older man will do the dishes when they’re done eating. 

Dean catches himself looking, then catches Cas looking at him looking and fuck. His admission of the night before comes stuttering back in and nearly makes him choke on his toast. Chuck looks startled and Cas grins behind his coffee mug, but Dean manages to wave off Chuck’s concern. 

“I’m good just. Wrong pipe,” he gasps, sucking down some coffee to clear his throat of crumbs. 

A quick call to check on Sam -  _ I’m fine, Dean, I’m 15, not a baby  _ \- Dean heads upstairs with Cas. Fucking is familiar and comfortable between them, Cas pinning Dean to the bed and pounding him into the mattress while Dean grits his teeth to hold back his moans. 

They pass the day in bed just like that, only venturing out under Chuck’s knowing look for more food and water. There’s no time to waste when Dean will definitely have to go home this evening; he’s never left Sammy alone for longer than 24 hours and Dad won’t be back from his job-of-the-week until Tuesday. 

Cas is panting beside Dean after their most recent round when he finally brings it up. 

“So. Are you going to try it?” 

It’s tempting to play dumb, but Dean knows exactly what Cas means. 

“That’s kinda messed up, don’t you think?” Weak, weak argument and Cas jabs him with one bony elbow. 

“Yeah, says the guy who popped his baby brother’s cherry.” 

And yeah. Good point. 

“It’s not like your dad will go for it anyway, man. He’s a pretty upstanding guy for raising a bunch of degenerates.” 

Cas laughs aloud at that. Just the sound makes Dean smile, and he’s grinning into the kiss Cas presses to his mouth. 

 

* * *

 

 

“You’re such a loser. Just go.” Sam’s sprawled out on the couch, watching Dean clean aimlessly. “Dad’ll be home soon, and you know he knows you’re screwing Cas.” 

“Feel like an asshole leaving you alone,” Dean mumbles back. 

 

Stretching so his spine pops, Sam grins mischievously at his brother. “Who says I’ll be alone?” 

 

“Little shit. Just use condoms okay? I’m not explaining to Dad that he’s gonna be a grandad or why you’ve got the clap.” 

 

Dean pointedly leaves a half box of condoms and a fresh bottle of lube on Sam’s bed before he leaves, ruffling the kid’s hair as he heads out the door. Cas meets him in the entry and whisks him upstairs. 

 

“Eager?” Dean laughs, draping his arms around Cas’ neck as the other boy undoes his belt and jeans. 

 

“You’ve no idea.” 

 

Escaping Cas’ hold, Dean steps out of his jeans and boxers and throws his shirt on the pile. He drapes himself over the bed, shoving a pillow beneath his hips and spreading his thighs. Cas is on him in an instant. One thumb dips down to brush at his hole, and Dean grins when he hears the pop of the lube cap. Cas only preps him briefly before the slick head of his cock is pushing at Dean’s hole. 

 

“C’mon,” Dean mutters, rocking back. “Fuck me, Cas.” 

 

A quick thrust in shoves a grunt from Dean’s throat. He fists his hands in the sheets and meets Cas for the next one. They’re not always so rough, but it feels good to let loose after a long week. Strong fingers dig at his hips, and Cas pumps his hips hard enough to send the headboard crashing against the wall. 

 

One of Cas’ hands pushes along Dean’s back, urging him down so his chest is pressed flat against the bed. The angle pushes his ass up and spreads him wider. He slides across the sheets for the first few thrusts, then braces his hands on the creaking headboard to brace himself. 

 

“F-fuck, Cas.” 

 

Dean’s gonna be sore tomorrow, bruised and aching and Sam will make fun of the extra bow in his legs, but he doesn’t give a shit. He’s getting close, body clenching tighter and highlighting the thickness of Cas’ cock. It drags his rim, tugging it out and shoving it in, tender skin that’ll be left hot and pink.

 

Nails dig into Dean’s back when Cas clenches his fingers, and the little zing of pain makes him yell, cock twitching and - 

 

“Cl-close.” He wants to beg and can’t get the air, but Cas slides his other hand from Dean’s hip to his dick anyway, stroking him quick and tight. Dean can’t keep himself from shoving back hard, choked cry in his throat when he comes. He whines when Cas lets go of his cock, but the sharp thrusts Cas pounds into him as he chases his own orgasm spark along his prostate enough to make up for it. 

 

The kiss Cas presses against his shoulder is incongruous to the rough fucking Dean’s just been given, but that’s Cas. He pulls out and collapses between Dean and the wall, sticky-soft cock against his thigh. 

 

“Damn, you weren’t joking about eager.” Dean’s words are muffled in the sheets. His ears are ringing a little the way they do after a particularly good orgasm. Cas dances his fingers along Dean’s arm and back, tracing scars and freckles in a soothing pattern.

 

“Dad’ll be home soon.” It sounds like an offhand comment, but Dean knows better. Sure enough, there’s a click of the door and rustling as Chuck settles in. “You should go down. He had a lot of meetings today about the new book. I’m sure he could use the stress relief.” 

 

Cas keeps his tone light, but the phrasing makes Dean shiver. Cas knows that Dean likes to be used, likes to be an outlet for other people’s frustrations. It’s always been what gets him off the hardest. 

 

“Shit, Cas. He - he’ll probably throw me out on my ass.” 

 

“Mm I don’t think so. He knows how fond I am of you. If anything, he’ll make himself scarce when you’re here.” 

 

_ Fond _ . Dean would blush if his face wasn’t already red. Yeah, Dean’s  _ fond _ of Cas, too. He’s never had a relationship this long, and the weekends he can’t be with Cas rub him the wrong way. 

 

“You’ll be awake when I come back?”

 

“Of course. I have a painting to work on. Besides, I’m kind of curious to see you in the aftermath.” 

 

Dean feels vulnerable, taking the stairs barefoot with the cool air of the house flowing over his skin. It highlights the wetness lingering between his cheeks, and he nearly chickens out before he can force himself to step through the door to the living room. Chuck’s ducked behind his computer where he sits at his writing desk, and Dean’s nearly close enough to touch before the man realizes he’s there. 

 

“Dean! Uh, what - why are you - I mean-” Chuck stutters. His eyes are wide behind his reading glasses, and the wheels of his office chair squeak as he rolls backwards despite the desk between them. He’s obviously struggling to keep his eyes on Dean’s face and yeah. There might be a better chance of this working than he thought. 

 

“Though you could use a little stress relief.” Dean quotes Cas, going for cocky and he almost makes it. It’s enough to have Chuck gulping and his eyes dancing downward briefly. “All you have to do is say no, and I’ll never ask again. But if you want it . . .” 

 

Chuck doesn’t speak, so Dean circles around the desk. The older man’s obviously looking at him now, eyes running up and down his legs and torso, lingering on his hardening cock. Dean leans against the edge of the desk, wishing Chuck had a sturdier chair so he could crawl right into the man’s lap, but he can improvise. 

 

“Tell me what you want, Chuck. You want me to suck you? Or do you wanna fuck me?” Dirty words earn Dean his first quiet moan, and he can’t keep the grin off of his face. On a whim, he turns around, nudging the open laptop to the side and spreading himself out on the desk. The wood’s cool and faintly sticky against his chest, dotted with rings of old condensation from Chuck’s booze. “I’m nice and open. Cas took care of that. Could just slide right in.” 

 

For a split second, Dean fears he’s pushed too far. Then, hesitant fingers just brush the soft skin of his ass. Squeaking wheels and creaking leather let him know that Chuck is finally on his feet, and, sure enough, warm hands settle on his cheeks. They’re calloused differently than Cas’ and it’s probably telling that Dean knows that. 

 

A clink of a belt and the buzz of a zipper makes his cock throb. Denim brushes the backs of his thighs as Chuck edges closer, and the warm length of the older man’s cock settles along Dean’s ass. 

 

“I-I don’t have-” 

 

“Don’t need lube. Cas-” - God, Dean feels filthy saying it for once - “- Cas left me nice and wet inside.” 

 

Chuck makes a wounded sound. He takes a moment to spit on his cock before he’s pushing in. Cas is thick, but Chuck is longer, and Dean’s toes curl against the rug at the depth.

 

“Oh,  _ shit _ .” 

 

There’s nothing for Dean to hang on to, fingers scrabbling at pock-marked wood. It takes Chuck a couple of thrusts before he gets all the way inside, and Dean will deny the little sob that escapes him when Chuck bottoms out until his dying day. 

 

Chuck doesn’t have half the power behind his thrusts that Cas does, but he certainly has the skill. He finds Dean’s prostate easily within a couple thrusts and keeps the slow and steady, which is almost excruciating to Dean’s tender hole and aching cock. There’s no way for Dean to get any real leverage bent over the desk like this, so all he can do is take it.

 

The thought of it shouldn’t be nearly that hot. 

 

“Please, Mr. Shurley.” 

 

Dean grunts at the sharp jab the words earn him, and he can feel Chuck start to lose it. He thrusts erratically, fingers digging into Dean’s hips. Punching deep, Chuck groans and Dean can almost sense the come flooding into him. He’s not close enough for it to get him off, but Chuck gathers himself enough to give Dean a reach-around. 

 

Come slips out of Dean’s hole when Chuck pulls out, some dripping down his sack and the rest making its way lazily down his thigh. Dean tries to catch his breath while Chuck tucks himself back in. He levers himself up to stand on shaky legs. Chuck is red-faced, but clearly sated; tension has melted from his shoulders and his eyes have that same haze that Cas gets when he’s just come. 

 

Chuck clears his throat and manages to make eye contact. “Are you okay?” 

 

“More than,” Dean grins lazily. “Thanks, Mr. Shurley.” He pretends not to see the shudder that runs through Chuck as he sidesteps the puddle of  come on the floor. More runs down his leg as he pads up the stairs, and Cas is on him the minute he’s through the door. 

 

“Fucked you sloppy,” Cas murmurs, pushing his fingers inside Dean. Cas fingers out as much as he can, dropping to his knees and shoving one of Dean’s legs up so he can lap at the mess. 

 

“Can’t go again,” Dean insists. Cas is lapping at his hole, chasing the taste of his father’s come and his own. 

 

Cas pulls back enough to breathe, “You don’t have to. Just let me.” 

 

Dean’s trembling by the time Cas is done, oversensitized and overwhelmed. He collapses gratefully on the bed, scooching over when Cas nudges him. 

 

“Wanna do that again.” 

 

“You can. Whenever you want. I just . . . want to hear about it. Want to clean it out of you.” 

 

Dean hums in acknowledgement, and wonders just what it would take to get Chuck to fuck Cas. 


End file.
